Advances on the Amaryllidacea Alkaloids Collected in South Africa, Andean South America and the Mediterranean Basin

Abstract

The alkaloids are one of the most represented family of natural occurring biological active compounds. Amaryllidaceae are also very well known for their beautiful flower and are thus used as ornamental plants in historic and public gardens. The Amaryllidacea alkaloids constitute an important group that is subdivided into different subfamilies with different carbon skeletons. They are well known from ancient times for their long application in folk medicine, and in particular, Narcissus poeticus L. was known to Hippocrates of Cos (ca. B.C. 460-370), who treated uterine tumors with a formulate prepared from narcissus oil. To date, more than 600 alkaloids of 15 chemical groups exhibiting various biological activities have been isolated from the Amaryllidaceae plants. This plant genus is diffused in regions of Southern Africa, Andean South America and the Mediterranean basin. Thus, this review describes the chemical and biological activity of the alkaloids collected in these regions in the last two decades as weel those of isocarbostyls isolated from Amaryllidaceae in the same regions and same period.

Keywords: Amaryllidacea; Andean South America; Mediterranean regions; South Africa; alkaloids; biological activity; chemistry; secondary metabolites.

Figure 1

Some representative Amaryllidaceae genera [2]: (A) Ammocharis coranica; (B) Boophone disticha; (C) Brunsvigia radulosa; (D) Clivia miniata; (E) Crinum delagoense; (F) Cyrtanthus contractus; (G) Gethyllis ciliaris; (H) Haemanthus albiflos; (I) Nerine filifolia; (J) Sternbergia lutea; (K) Pancratium maritimum; (L) Narcissus tazetta; (M) Amaryllis belladonna. The pictures are original photos obtained by the author.

Figure 2

Alkaloids produced by Andean Amaryllidaceae plants: Habranthus jamesonii, Phycella herbertiana, Rhodophiala mendocina and Zephyranthes filifolia (1–6) H. jamesonii and P. herbertiana (7 and 8), Caliphruria subedentata (1, 2, 5, and 10–16 and 18, 19 and 21), Hippeastrum papilio (2, 5, 14, 24 and 25) and Rhodolirium andicola (2, 5, 6, 18, 21, 28–30 and 32, 34) Crinum amabile, Crinum erubescens, Crinum moorei, Amaryllis belladonna and Zephyranthes carinata (1, and 35), Pyrolirion albicans (2, 4, and 38, 42 and 43), Amaryllis belladonna (44), and Ismene amancaes (1, 2, 6, 7, and 42 and 48–50).

Figure 3

Alkaloids produced by Caliphruria subedentata (17, 20), Hippeastrum papilio (22, 23, 26 and 27) and Rhodolirium andicola (31 and 33) Crinum amabile, Crinum erubescens, Crinum moorei, Amaryllis belladonna and Zephyranthes carinata (20, 33, and 36), Pyrolirion albicans (37 and 39), Amaryllis belladonna (45–47), Hippeastrum stapfianum (47), and Ismene amancaes (17, 20 and 51).

Figure 4

Alkaloids produced by South Africa Amaryllidaceae plants: Boophone haemanthoides (52–60), Nerine sarniensis (61–64), Boophone disticha (65–67), Crinum buphanoides (68), Crinum graminicola (69), Sceletium tortuosum (70), Haemanthus humilis (71), Ammocharis coranica (75, 77–79 and 81), and Clivia miniata (86).

Figure 5

Alkaloids produced by South Africa Amaryllidaceae plants: Haemanthus humilis (72 and 73), Crinum moorei (74), Ammocharis coranica (76, 80 and 81), and Clivia miniata (82–85 and 87–89).

Figure 6

Alkaloids produced by Mediterranean Amaryllidaceae plants: Pancratium maritimum (90–93), Narcissus serotinus L. (94–101), and Narcissus triandrus (102–107).

Figure 7

Alkaloids produced by Mediterranean Amaryllidaceae plants: Narcissus triandrus (108 and 109) and Lapiedra martinezii (110–121).

Figure 8

Alkaloids produced by Mediterranean Amaryllidaceae plants: Pancratium illyricum L. (122–127), Narcissus jonquilla quail (128), Clivia nobilis (129 and 130), and Galanthus elwesii (131–138).

Figure 9

Alkaloids produced by Mediterranean Amaryllidaceae plants: Galanthus elwesii (138), Narsissus tazetta a subsp. tazetta (139), Pancratium maritimum (140–142), and Galanthus fosteri (143–146).

Figure 10

Isocarbostyryl isolated from Pancratium maritimum, Nerine sarniensis, Crinum jagus, and Crinum buphanoides (147), Narcissus pseudonarcissus and Sternbergia lutea (152), Hymenocallis littoralis and Boophane haemanthoides (153), Narcissus serotinus (154), Crinum buphanoide (155–157), and Crinum latifolium and Crinum pretense (147 and 155–157). Alkaloids isolated from C. jagus (148–151).